10,12-dimethoxy-1-(methoxymethoxy)-6-oxo-6H-dibenzo[c,h]chromene-8-carbaldehyde | 1395924-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 10,12-dimethoxy-1-(methoxymethoxy)-6-oxo-6H-dibenzo[c,h]chromene-8-carbaldehyde
• 英文别名: 10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]-naphtho[1,2-b]pyran-6-one-8-carbaldehyde；10,12-Dimethoxy-1-(methoxymethoxy)-6-oxonaphtho[1,2-c]isochromene-8-carbaldehyde；10,12-dimethoxy-1-(methoxymethoxy)-6-oxonaphtho[1,2-c]isochromene-8-carbaldehyde
• CAS: 1395924-05-6
• 化学式: C₂₂H₁₈O₇
• 分子量: 394.381
• InChiKey: ZFJFUBGIAHCYDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  10,12-dimethoxy-1-(methoxymethoxy)-6-oxo-6H-dibenzo[c,h]chromene-8-carbaldehyde 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到1-hydroxy-10,12-dimethoxy-6H-benzo[d]naphtho[1,2-b]-pyran-6-one-8-carboxaldehyde
  参考文献：
  名称：

  An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues

  摘要：

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.

  DOI：

  10.1021/jo3012682
• 作为产物：
  描述：

  1,5-二羟基萘 在 哌啶 、 吡啶 、 borane dimethyl sulfide complex 、 氧气 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 copper(l) chloride 、 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 97.66h， 生成 10,12-dimethoxy-1-(methoxymethoxy)-6-oxo-6H-dibenzo[c,h]chromene-8-carbaldehyde
  参考文献：
  名称：

  An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues

  摘要：

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.

  DOI：

  10.1021/jo3012682

文献信息

• Carbene-Catalyzed Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of Defucogilvocarcins
  作者：Xuan Huang、Tingshun Zhu、Zhijian Huang、Yuexia Zhang、Zhichao Jin、Giuseppe Zanoni、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.7b03102

  日期：2017.11.17

  An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M

  据报道，在烯醛和呋喃酮之间的N杂环卡宾催化的正式[5 + 5]反应可在一个步骤中生成多取代的香豆素。每个底物中的五个原子参与该催化过程以形成苯和内酯环。该方法的功效在以香豆素为关键结构基序的几种天然产物（去甲福尔霉素M，E和V）的无金属全合成中得到了进一步证明。
• An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues
  作者：Penchal Reddy Nandaluru、Graham J. Bodwell

  DOI：10.1021/jo3012682

  日期：2012.9.21

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.